8-alkoxyquinolonecarboxylic acid and salts thereof

Abstract

Quinolonecarboxylic acid derivatives of the following formula: <IMAGE> wherein R indicates a hydrogen atom or lower alkyl group, R1 indicates a lower alkyl group, R2 indicates a hydrogen atom, amino group or nitro group, X indicates a halogen atom, and Z indicates a halogen atom, piperazino group, N-methylpiperazino group, 3-methylpiperazino group, 3-hydroxypyrrolidino group, or pyrrolidino group of the following formula, <IMAGE> (here, n is 0 or 1, R3 indicates a hydrogen atom or lower alkyl group, R4 indicates a hydrogen atom, lower alkyl group and R5 indicates a hydrogen atom, lower alkyl group, acyl group or alkoxycarbonyl group), the hydrates and pharmaceutically acceptable salts thereof are useful as antibacterial agents.

What is claimed is: 
     
       1. 8-Alkoxyquinolonecarboxylic acid derivatives represented by a general formula (I); ##STR27## wherein R indicates a hydrogen atom or lower alkyl group, R 1  indicates a lower alkyl group, R 2  indicates a hydrogen atom X indicates a halogen atom, and Z indicates a halogen atom, piperazino group, N-methylpiperazino group, 3-methylpiperazino group, 3-hydroxypyrrolidino group, or pyrrolidino group of the following formula, ##STR28## where, n is 0 or 1, R 3  indicates a lower alkylgroup, R 4  indicates a hydrogen atom, lower alkyl group, hydroxy-substituted lower alkyl group or halogenated lower alkyl group and R 5  indicates a hydrogen atom, lower alkyl group, acyl group or alkoxycarbonyl group, the hydrates or the pharmaceutically acceptable acid addition or alklai salts thereof. 
     
     
       2. 8-Alkoxyquinolonecarboxylic acid derivative as claimed in claim 1, wherein said derivative is 1-cyclopropyl-6-fluoro-1,4-dihydro-8-methoxy-4-oxo-7-(1-piperazinyl)-3-quinolinecarboxylic acid. 
     
     
       3. 8-Alkoxyquinolonecarboxylic acid derivative as claimed in claim 1, wherein said derivative is 1-cyclopropyl-6-fluoro-1,4-dihydro-8-methoxy-7-(4-methyl-1-piperazinyl)-4-oxo-3-quinolinecarboxylic acid. 
     
     
       4. 8-Alkoxyquinolonecarboxylic acid derivative as claimed in claim 1, wherein said derivative is 1-cyclopropyl-6-fluoro-1,4-dihydro-8-methoxy-7-(3-methyl-1-piperazinyl)-4-oxo-3-quinolinecarboxylic acid. 
     
     
       5. 8-Alkoxyquinolonecarboxylic acid derivative as claimed in claim 1, wherein said derivative is 7-(cis-3-amino-4-methyl-1-pyrrolidinyl)-1-cyclopropyl-6-fluoro-1,4-dihydro-8-methoxy-4-oxo-3-quinolinecarboxylic acid. 
     
     
       6. 8-Alkoxyquinolonecarboxylic acid derivative as claimed in claim 1, wherein said derivative is 7-(trans-3-amino-4-methyl-1-pyrrolidinyl)-1-cyclopropyl-6-fluoro-1,4-dihydro-8-methoxy-4-oxo-3-quinolinecarboxylic acid. 
     
     
       7. 8-Alkoxyquinolonecarboxylic acid derivative as claimed in claim 1, wherein said derivative is 7-(3-amino-4-methyl-1-pyrrolidinyl)-1-cyclopropyl-6-fluoro-1,4-dihydro-8-methoxy-4-oxo-3-quinolinecarboxylic acid. 
     
     
       8. 8-Alkoxyquinolonecarboxylic acid derivative as claimed in claim 1, wherein said derivative is 1-cyclopropyl-6-fluoro-1,4-dihydro-8-ethoxy-4-oxo-7-(1-piperazinyl)-3-quinolinecarboxylic acid.